Dimethyl Sulfide → HCID 68459038, compound

HRID 2356984Notes

Reaction equation

HRID 2356984 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([S:8]([C:11]2[CH:20]=[C:19]3[C:14]([CH:15]([CH2:21][C:22](O)=[O:23])[CH2:16][CH2:17][O:18]3)=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.S(C)C>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([S:8]([C:11]2[CH:20]=[C:19]3[C:14]([CH:15]([CH2:21][CH2:22][OH:23])[CH2:16][CH2:17][O:18]3)=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 1068Dimethyl SulfideHCID 58668700HCID 58668700, compound

Product 1

HCID 68459038HCID 68459038, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [7-(3-Fluoro-benzenesulfonyl)-chroman-4-yl]-acetic acid (1.5 g, 4.28 mmol) in THF 40 ml) was added BH3 Me2S (0.41 ml, 4.32 mmol) at 0° C. The mixture was stirred in the ice bath for 30 minutes and then at room temperature overnight. The mixture was quenched with MeOH and the solvent was removed. The residue was dissolved in EtOAc, washed with brine, dried with MgSO4, filtered and concentrated to give 2-[7-(3-Fluoro-benzenesulfonyl)-chroman-4-yl]-ethanol as a clear syrup: 1.35 g; MS: 337.2 (M+H)+, 378.2(M+CH3CN+H)+.

Workup

  1. customat room temperature
  2. customovernight
  3. customThe mixture was quenched with MeOH
  4. customthe solvent was removed
  5. dissolutionThe residue was dissolved in EtOAc
  6. washwashed with brine
  7. dry with materialdried with MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-c1979b82c6a049fe9fc2db9428dd6676
Source dataset
uspto-grants-2010_07
Patent number
US07759389B2

Reaction notes

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